Aminoacetonitrile derivative agricultural and horticultural insecticide containing the same and use thereof

ABSTRACT

An aminoacetonitrile derivative of the formula (I):                    
     (wherein Ar 1  and Ar 2  represents phenyl group; substituted phenyl group having at least one subsituent selected from halogen atom, nitro group, cyano group, (halo) C 1 -C 6  alkyl group, (halo) C 1 -C 6  alkoxyl group, (substituted) pheny group, (substituted) phenyloxy group and (substituted) phenylacetylene group; (substituted) pyridyl group; and (substituted) naphthyl group, Q represents —C(R 1 )(R 2 )— (wherein R 1  and R 2  represent hydrogen atom, halogen atom, (halo) C 1 -C 6  alkyl group, (halo) C 1 -C 6  alkoxy group, (substituted) C 3 -C 6  cycloalkyl group), or R 1  and R 2  may be bound to represent C 2 -C 6  alkylene group), —CH═CH— or —C≡C—, d is 0 or an integer of 1, R 3  represents hydrogen atom, (halo) C 1 -C 6  alkyl group, R 4 , R 5 , R 6 , R 7  and R 8  represent hydrogen atom, halogen atom, (halo) C 1 -C 6  alkyl group, W is —O—, —S—, —SO 2 — or —N(R 9 )— (wherein R 9  is a hydrogen atom or C 1 -C 6  alkyl group), and a and b are 0 or an integer of 1 to 4)), an agricultural and hortecultural insecticide containing as an active ingredient said derivative, and a method for using the insecticide.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to an aminoacetonitrile derivative of theformula (I) and to an agricultural and horticultural insecticidecontaining the said derivative as an active ingredient. The presentinvention also relates to a method for using the insecticide.

2. Description of the Related Art

Japanese Patent Application Laid-open No. Hei 9-48750 (1997) discloses aphenylalkanoic acid amide derivative as an agricultural andhorticultural fungicide, Japanese Patent Application Laid-open No. Hei6-220004 (1994) discloses N-phenylacetaminonitriles as intermediates inproduction, and Japanese Patent Applications Laid-opens No. Hei 6-263731(1994), No. Hei 6-271537 (1994) and No. Hei 7-252222 (1995) disclosecompounds similar to the aminoacetonitrile derivative of the formula (I)of the present invention.

SUMMARY OF THE INVENTION

With view to developing novel agricultural and horticulturalinsecticide, the present inventors have made intensive research and as aresult, they have now found that an aminoacetonitrile derivative of theformula (I) is a novel compound and has a remarkable insecticidaleffect, thus completing the present invention.

DETAILED DESCRIPTION OF THE INVENTION

The present invention relates to an aminoacetonitrile derivative of theformula (I) and to an agricultural and horticultural insecticidecontaining said derivative as an active ingredient:

(wherein Ar¹ and Ar² may be the same or different and each represents aphenyl group;

a substituted phenyl group having at least one substituent which may bethe same or different and selected from the group of

a halogen atom, a nitro group, a cyano group,

a C₁-C₆ alkyl group, a halo C₁-C₆ alkyl group,

a C₁-C₆ alkoxy group, a halo C₁-C₆ alkoxy group,

a C₂-C₆ alkenyl group, a halo C₂-C₆ alkenyl group,

a C₂-C₆ alkynyl group, a C₃-C₆ cycloalkyl group,

a C₂-C₆ alkenyloxy group, a halo C₂-C₆ alkenyloxy group,

a C₁-C₆ alkylthio group, a halo C₁-C₆ alkylthio group,

a C₁-C₆ alkylsulfonyloxy group,

a halo C₁-C₆ alkylsulfonyloxy group,

a C₁-C₆ alkylsulfinyl group,

a halo C₁-C₆ alkylsulfinyl group,

a C₁-C₆ alkylsulfonyl group,

a halo C₁-C₆ alkylsulfonyl group,

a C₂-C₆ alkenylthio group,

a halo C₂-C₆ alkenylthio group,

a C₂-C₆ alkenylsulfinyl group,

a halo C₂-C₆ alkenylsulfinyl group,

a C₂-C₆ alkenylsulfonyl group,

a halo C₂-C₆ alkenylsulfonyl group,

a C₁-C₆ alkylamino group, a di-C₁-C₆ alkylamino group,

a C₁-C₆ alkylsulfonylamino group,

a halo C₁-C₆ alkylsulfonylamino group,

a C₁-C₆ alkylcarbonyl group,

a halo C₁-C₆ alkylcarbonyl group,

a C₁-C₆ alkyloxycarbonyl group,

a phenyl group,

a substituted phenyl group having at least one substituent which may bethe same or different and selected from the group consisting of ahalogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a haloC₁-C₆ alkyl group, a C₁-C₆ alkoxy group, a halo C₁-C₆ alkoxy group, aC₁-C₆ alkylthio group, a halo C₁-C₆ alkylthio group, a C₁-C₆alkylsulfinyl group, a halo C₁-C₆ alkylsulfinyl group, a C₁-C₆alkylsulfonyl group and halo C₁-C₆ alkylsulfonyl group,

a phenyloxy group,

a substituted phenyloxy group having on the ring thereof at least onesubstituent which may be the same or different and selected from thegroup consisting of a halogen atom, a cyano group, a nitro group, aC₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₆ alkoxy group, ahalo C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo C₁-C₆ alkylthiogroup, a C₁-C₆ alkylsulfinyl group, a halo C₁-C₆ alkylsulfinyl group, aC₁-C₆ alkylsulfonyl group and a halo C₁-C₆ alkylsulfonyl group,

a phenylacetylene group,

a substituted phenylacetylene group having on the ring thereof at leastone substituent which may be the same or different and selected from thegroup consisting of a halogen atom, a cyano group, a nitro group, aC₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₆ alkoxy group, ahalo C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo C₁-C₆ alkylthiogroup, a C₁-C₆ alkylsulfinyl group, a halo C₁-C₆ alkylsulfinyl group, aC₁-C₆ alkylsulfonyl group and a halo C₁-C₆ alkylsulfonyl group,

a pyridyloxy group and

a substituted pyridyloxy group having on the ring thereof at least onesubstituent which may be the same or different and selected from thegroup consisting of a halogen atom, a cyano group, a nitro group, aC₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₆ alkoxy group, ahalo C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo C₁-C₆ alkylthiogroup, a C₁-C₆ alkylsulfinyl group, a halo C₁-C₆ alkylsulfinyl group, aC₁-C₆ alkylsulfonyl group and a halo C₁-C₆ alkylsulfonyl group;

a pyridyl group;

a substituted pyridyl group having on the ring thereof at least onesubstituent which may be the same or different and selected from thegroup consisting of a halogen atom, a cyano group, a nitro group, aC₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₆ alkoxy group, ahalo C₁-C₆ alkoxy group, a C₂-C₆ alkenyloxy group, a halo C₂-C₆alkenyloxy group, a C₁-C₆ alkylthio group, a halo C₁-C₆ alkylthio group,a C₁-C₆ alkylsulfinyl group, a halo C₁-C₆ alkylsulfinyl group, a C₂-C₆alkenylthio group, a halo C₂-C₆ alkenylthio group, a C₂-C₆alkenylsulfinyl group, a halo C₂-C₆ alkenylsulfinyl group, a C₁-C₆alkylsulfonyl group, a halo C₁-C₆ alkylsulfonyl group, a C₂-C₆alkenylsulfonyl group, a halo C₂-C₆ alkenylsulfonyl group, a C₁-C₆alkylamino group and a di-C₁-C₆ alkylamino group;

a naphthyl group; or

a substituted naphthyl group having on the ring at least one substituentwhich may be the same or different and selected from the groupconsisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₆ alkoxy group, a haloC₁-C₆ alkoxy group, a C₂-C₆ alkenyloxy group, a halo C₂-C₆ alkenyloxygroup, a C₁-C₆ alkylthio group, a halo C₁-C₆ alkylthio group, a C₁-C₆alkylsulfinyl group, a halo C₁-C₆ alkylsulfinyl group, a C₁-C₆alkylsulfonyl group, a halo C₁-C₆ alkylsulfonyl group, a C₂-C₆alkenylthio group, a halo C₂-C₆ alkenylthio group, a C₂-C₆alkenylsulfinyl group, a halo C₂-C₆ alkenylsulfinyl group, a C₂-C₆alkenylsulfonyl group, a halo C₂-C₆ alkenylsulfonyl group, a C₁-C₆alkylamino group and a di-C₁-C₆ alkylamino group;

Q represents a group of

(wherein R¹ and R² may be the same or different and each represent ahydrogen atom, a halogen atom, a C₁-C₆ alkyl group, a halo C₁-C₆ alkylgroup, a C₁-C₆ alkoxy group, a halo C₁-C₆ alkoxy group, a C₃-C₆cycloalkyl group or a substituted C₃-C₆ cycloalkyl group having at leastone substituent which may be the same or different and selected from thegroup consisting of a halogen atom and a C₁-C₆ alkyl group, and R¹ andR² may be bound to represent a C₂-C₆ alkylene group which may have onits chain at least one substituent selected from the group consisting ofa halogen atom, a C₁-C₆ alkyl group and a C₁-C₆ alkoxy group), —CH═CH—or —C≡C—; d is 0 or an integer of 1;

R³ represents a hydrogen atom, a C₁-C₆ alkyl group, a halo C₁-C₆ alkylgroup, a cyano C₁-C₆ alkyl group, a C₁-C₆ alkylthio group, a halo C₁-C₆alkylthio group, a C₂-C₆ alkenyl group or a C₂-C₆ alkynyl group;

R⁴, R⁵, R⁶, R⁷ and R⁸ which may be the same or different and eachrepresents a hydrogen atom, a halogen atom, a C₁-C₆ alkyl group, a haloC₁-C₆ alkyl group, a C₃-C₆ cycloalkyl group or a substituted C₃-C₆cycloalkyl group having at least one substituent which may be the sameor different and selected from the group consisting of a halogen atomand a C₁-C₆ alkyl group, a phenyl group or a substituted phenyl grouphaving at least one substituent group which may be the same or differentand selected from the group consisting of a halogen atom, a nitro group,a cyano group, a C₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₆alkoxy group, a halo C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a haloC₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo C₁-C₆alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo C₁-C₆alkylsulfonyl group, a C₁-C₆ alkylamino group and a di-C₁-C₆ alkylaminogroup, and R⁴ and R⁵ together may form a C₁-C₆ alkylene group;

W is —O—, —S—, —SO₂—, or —N(R⁹)— (wherein R⁹ represents a hydrogen atomor a C₁-C₆ alkyl group), and

a and b may be the same or different and are 0 or an integer of 1 to4)).

In the present invention, preferred substituents of theaminoacetonitrile derivative of the formula (I) contain, for example, aphenyl group as the substituent for Ar¹ and Ar², a halogen atom, a haloC₁-C₆ alkyl group and a halo C₁-C₆ alkoxy group as the substituent onthe ring of Ar¹ and Ar², a hydrogen atom as the substituent for R¹, R²,R³, R⁵ and R⁶, a C₁-C₆ alkyl group as the substituent for R⁴, —CH₂— asthe substituent for Q, —O— as the substituent for W, and a is preferablyan integer of 1 and b is preferably 0.

The aminoacetonitrile derivative of the formula (I) of the presentinvention contains compounds having stereoisomers and the presentinvention contains such stereoisomers too.

The aminoacetonitrile derivative of the formula (I) of the presentinvention can be produced, for example, by the following productionmethod.

wherein R³, R⁴, R⁵, R⁶, R⁷, R⁸, Ar¹, Ar², Q, W, a, b, and d have thesame meanings as described above, M represents an alkali metal atom, andHal represents a halogen atom.)

1. Formula (IV)→Formula (I)

The aminoacetonitrile derivative of the formula (I) can be produced byreacting aminoacetonitrile derivatives of the formula (IV) with acidhalides of the formula (III) in the presence of a base (for example,triethylamine, pyridine, etc.). The aminoacetonitrile derivative of theformula (I) can also be produced by condensation-reactingaminoacetonitriles of the formula (IV) with acids of the formula (II) byuse of a condensing agent (for example, dicyclohexylcarbodiimide,2-chloro-1-methylpyridiniumiodide, etc.). The acids of the formula (II)can be produced by known methods (for example, J. Org. Chem. 763, 1948,Organic Synthesis Coll., Vol. 1, 436, J. Org. Chem. 763, 1948, OrganicSynthesis Coll., Vol. 1, 336, Beilsteins Handbuch 9, 573, BeilsteinsHandbuch 9, 633, etc.).

2. Formula (VII)→Formula (IV)

The aminoacetonitriles of the formula (IV) can be produced, for example,by the reaction of carbonyl compounds of the formula (VII) with metalcyanides of the formula (VI) (for example, sodium cyanide, potassiumcyanide, etc.) with amines of the formula (V). As the CN source, organiccyanides such as trimethylsilylnitrile and acetonecyanohydrin can beused. These reactions are a method known as Strecker reaction (forexample, Formation of C—C Bonds Vol. 1, Georg Thieme Publishers 1973,Organic Synthesis Coll. Vol., 3, 88, etc.).

The carbonyl compounds of the (VII) can be produced, for example, by thefollowing production method.

wherein R³, R⁴, R⁵, R⁶, R⁷, R⁸, Ar¹, Ar², a and b have the same meaningsas described above, L represents a leaving group such as a halogen atom,a methylsulfonyloxy group or a p-methylbenzenesulfonyloxy group, W′ isOH, SH or NHR⁹ (where R⁹ has the same meaning as described above, Rs areC₁-C₆ alkyl groups which may be the same or different and represent aC₁-C₄ alkylene group, or Rs together form a C₁ 14 C₄ alkylene group.

The carbonyl compounds of the formula (VII) can be produced, forexample, by reacting a compound of the formula (VIII-1) having a leavinggroup L with a compound of the formula (IX-1) in the presence of a base.

Similarly, the carbonyl compounds of the formula (VII) can also beproduced by reacting a compound of the formula (VIII-2) with a compoundof the formula (IX-2).

Moreover, the carbonyl compounds of the formula (VII) can be produced bydeprotection-reacting a compound of the formula (XII) derived byreacting a compound of the formula (X-1) whose carbonyl group isprotected in the form of acetal, ketal or the like with a compound ofthe formula (IX-1), under acidic conditions. Similarly, the compounds ofthe formula (XII) can be produced by reacting a compound of the theformula (X-2) with a compound of the formula (IX-2). Further, thecarbonyl compounds of the formula (VII) can be produced by oxidizing acompound of the formula (XIII) derived by reacting an alcohol compoundof the formula (XI-1) with a compound of the formula (IX-1) with using asuitable oxidizing agent (for example, potassium permanganate, etc.).Similarly, the compound of the formula (XIII) can be produced byreacting an alcohol compound of the formula (XI-2) with a compound theformula (IX-2).

Typical compounds of the aminoacetonitrile derivative of the formula (I)of the present invention are shown in Tables 1, 2 and 3.

Formula (I)

TABLE 1 (R⁶═R⁷═R⁸═H, Q═—C(R¹)(R²)—,  d═1, b═0 (provided that thosedescribed are excepted) No. Ar¹ Ar² R¹ R² R³ R⁴ R⁵ W a 1 Ph Ph (CH₂)₂ HCH₃ H O 1 2 Ph 4-Cl—Ph H H H CH₃ H O 1 3 Ph 4-Cl—Ph (CH₂)₂ H CH₃ H O 1 4Ph 4-CF₃—Ph H H H CH₃ H O 1 5 Ph 4-CHF₂O—Ph H H W CH₃ H O 1 6 Ph4-CF₃O-Ph H H H CH₃ H O 1 7 Ph 4-CF₃S-Ph H H H CH₃ H O 1 8 Ph 4-CF₃SO₂—H H H CH₃ H O 1 Ph 9 Ph 4-Cl—Ph CH₃O H H CH₃ H O 1 10 2-Cl—Ph 2-Cl—Ph HH H CH₃ H O 4 11 2-Cl—Ph 4-Cl—Ph H H H CH₃ H O 2 b = 1 12 2-Cl—Ph4-Cl—Ph H H H H H O 1 13 2-Cl—Ph 4-Cl—Ph H H H CH₃ H O 1 14 2-Cl—Ph4-Cl—Ph H H H CH₃ CH₃ O 1 15 2-Cl—Ph 4-Cl—Ph H H H CH₃ CH₃ O 1 162-Cl—Ph 4-Cl—Ph H H H CH₃ n-C₃H₇ O 1 17 2-Cl—Ph 4-Cl—Ph H H H CH₃ n-C₃H₇O 1 18 2-Cl—Ph 4-Cl—Ph H H H CH₃ n-C₄H₉ O 1 19 2-Cl—Ph 4-Cl—Ph H H H CH₃n-C₄H₉ O 1 20 2-Cl—Ph 4-Cl—Ph H H H CH₃ H O 4 21 2-Cl—Ph 4-Cl—Ph H H HC₂H₅ H O 1 22 2-Cl—Ph 4-Cl—Ph H H H n-C₃H₇ H O 1 23 2-Cl—Ph 4-Cl—Ph H HH i-C₃H₇ H O 1 24 2-Cl—Ph 4-Cl—Ph H H H c-C₃H₅ H O 1 25 2-Cl—Ph 4-Cl—PhH H H t-C₄H₉ H O 1 26 2-Cl—Ph 4-Cl—Ph H H H (CH₂)₄ O 1 27 2-Cl—Ph4-Cl—Ph H H CH₃ CH₃ H O 1 28 2-Cl—Ph 4-Cl—Ph H H C₂H₅ CH₃ H O 1 292-Cl—Ph 4-Cl—Ph H H n-C₄H₉ CH₃ H O 1 30 2-Cl—Ph 4-Cl—Ph H H CH₂C≡CH CH₃H O 1 31 2-Cl—Ph 4-CF₃—Ph H H H CH₃ H O 1 32 2-Cl—Ph 4-CF₃—Ph H H H CH₃H O 1 33 2-Cl—Ph 4-CF₃O—Ph H H H CH₃ H O 1 34 2-Cl—Ph 4-CHF₂O—Ph H H HCH₃ H O 1 35 2-Cl—Ph 4-CF₃S—Ph H H H CH₃ H O 1 36 2-Cl—Ph 4-CF₃SO₂—Ph HH H CH₃ H O 1 37 2-F—Ph 4-CF₃O—Ph H H H CH₃ H O 1 38 2-F—Ph 4-CHF₂O—Ph HH H CH₃ H O 1 39 2-F—Ph 4-CF₃S—Ph H H H CH₃ H O 1 40 2-F—Ph 4-CF₃SO₂—PhH H H CH₃ H O 1 41 2-F—Ph 4-Cl—Ph H H H CH₃ H O 1 42 2-F—Ph 4-Cl—Ph(CH₂)₂ H CH₃ H O 1 43 2-F—Ph 4-CF₃—Ph H H H CH₃ H O 1 44 3-Cl—Ph 4-Cl—PhH H H CH₃ CH₃ O 1 45 3-Cl—Ph 4-Cl—Ph H H H CH₃ CH₃ O 1 46 3-Cl—Ph4-Cl—Ph H H H CH₃ n-C₃H₇ O 1 47 3-Cl—Ph 4-Cl—Ph H H H CH₃ n-C₃H₇ O 1 483-Cl—Ph 4-Cl—Ph H H H C₂H₅ H O 1 49 3-Cl—Ph 4-Cl—Ph H H H CH₃ H O 1 503-Cl—Ph 4-Cl—Ph H H H CH₃ H O 4 51 3-Cl—Ph 4-Cl—Ph H H H n-C₃H₇ H O 1 523-Cl—Ph 4-Cl—Ph H H H i-C₃H₇ H O 1 53 3-Cl—Ph 4-Cl—Ph H H H c-C₃H₅ H O 154 3-Cl—Ph 4-Cl—Ph H H H t-C₄H₉ H O 1 55 3-Cl—Ph 4-Cl—Ph H H H (CH₂)₄ O1 56 3-Cl—Ph 4-Cl—Ph (CH₂)₂ H CH₃ H O 1 57 4-Cl—Ph Ph H H H CH₃ H O 1 584-Cl—Ph Ph H H H CH₃ H S 1 59 4-Cl—Ph Ph H H H CH₃ H SO₂ 1 60 4-Cl—Ph2-Cl—Ph H H H CH₃ H O 1 61 4-Cl—Ph 2-Cl—Ph H H H CH₃ H O 4 62 4-Cl—Ph3-Cl—Ph H H H CH₃ H O 1 63 4-Cl—Ph 4-Cl—Ph H H H H H O 1 64 4-Cl—Ph4-Cl—Ph H H H CH₃ H O 1 65 4-Cl—Ph 4-Cl—Ph H H H CH₃ H O 2 b = 1 664-Cl—Ph 4-Cl—Ph H H H CH₃ H S 1 67 4-Cl—Ph 4-Cl—Ph H H H CH₃ H SO₂ 1 684-Cl—Ph 4-Cl—Ph H H H CH₃ H O 4 69 4-Cl—Ph 4-Cl—Ph H H H CH₃ CH₃ O 1 704-Cl—Ph 4-Cl—Ph H H H CH₃ n-C₃H₇ O 1 71 4-Cl—Ph 4-Cl—Ph H H H CH₃ n-C₄H₉O 1 72 4-Cl—Ph 4-Cl—Ph H H H CH₃ CF₃ O 1 73 4-Cl—Ph 4-Cl—Ph H H H C₂H₅ HO 1 74 4-Cl—Ph 4-Cl—Ph H H H n-C₃H₇ H O 1 75 4-Cl—Ph 4-Cl—Ph H H Hi-C₃H₇ H O 1 76 4-Cl—Ph 4-Cl—Ph H H H c-C₃H₅ H O 1 77 4-Cl—Ph 4-Cl—Ph HH H t-C₄H₉ H O 1 78 4-Cl—Ph 4-Cl—Ph H H H CF₃ H O 1 79 4-Cl—Ph 4-Cl—Ph HH H (CH₂)₄ O 1 80 4-Cl—Ph 4-Cl—Ph H H CH₃ CH₃ H O 1 81 4-Cl—Ph 4-Cl—Ph HH C₂H₅ CH₃ H O 1 82 4-Cl—Ph 4-Cl—Ph H H n-C₄H₉ CH₃ H O 1 83 4-Cl—Ph4-Cl—Ph H H CH₂C≡CH CH₃ H O 1 84 4-Cl—Ph 4-Cl—Ph CH₃ CH₃ H CH₃ H O 1 854-Cl—Ph 4-Cl—Ph i-C₃H₇ H H CH₃ H O 1 86 4-Cl—Ph 4-Cl—Ph i-C₃H₇ H H CH₃ HO 1 87 4-Cl—Ph 4-Cl—Ph CF₃ H H CH₃ H O 1 88 4-Cl—Ph 4-Cl—Ph (CH₂)₂ H CH₃H O 1 89 4-Cl—Ph 4-Cl—Ph (CH₂) H CH₃ H O 1 90 4-Cl—Ph 4-Cl—Ph (CH₂)₄ HCH₃ H O 1 91 4-Cl—Ph 4-Cl—Ph F F H CH₃ H O 1 92 4-Cl—Ph 4-I-Ph H H H CH₃H O 1 93 4-Cl—Ph 4-Br-Ph H H H CH₃ H O 1 94 4-Cl—Ph 4-F—Ph H H H CH₃ H O1 95 4-Cl—Ph 3-CF₃—Ph H H H CH₃ H O 1 96 4-Cl—Ph 4-CF₃—Ph H H H CH₃ H O1 97 4-Cl—Ph 4-C₂F₅—Ph H H H CH₃ H O 1 98 4-Cl—Ph 4-i-C₃F₇—Ph H H H CH₃H O 1 99 4-Cl—Ph 4-CF₃—Ph (CH₂)₂ H CH₃ H O 1 100 4-Cl—Ph 4-n-C₃F₇—Ph H HH CH₃ H O 1 101 4-Cl—Ph 4-CH₃—Ph H H H CH₃ H O 1 102 4-Cl—Ph 4-t-C₄H₉—PhH H H CH₃ H O 1 103 4-Cl—Ph 4-(t-C₄H₉ H H H CH₃ H O 1 —C≡C)—Ph 1044-Cl—Ph 4-CH₃O—Ph H H H CH₃ H O 1 105 4-Cl—Ph 4-CF₃O—Ph H H H CH₃ H O 1106 4-Cl—Ph 4-CHF₂O—Ph H H H CH₃ H O 1 107 4-Cl—Ph 4-CF₃SO₂—Ph H H H CH₃H O 1 108 4-Cl—Ph 4-CH₃S—Ph H H H CH₃ H O 1 109 4-Cl—Ph 4-CH₃SO₂—Ph H HH CH₃ H O 1 110 4-Cl—Ph 4-CF₃S—Ph H H H CH₃ H O 1 111 4-Cl—Ph4-CF₃SO₂—Ph H H H CH₃ H O 1 112 4-Cl—Ph 4-CHF₂S—Ph H H H CH₃ H O 1 1134-Cl—Ph 4-CHF₂SO₂—Ph H H H CF₃ H O 1 114 4-Cl—Ph 4-n-C₃F₇S—Ph H H H CH₃H O 1 115 4-Cl—Ph 4-i-C₃F₇S—Ph H H H CH₃ H O 1 116 4-Cl—Ph4-n-C₃F₇SO₂—Ph H H H CH₃ H O 1 117 4-Cl—Ph 4-n-C₆F₁₃S—Ph H H H CH₃ H O 1118 4-Cl—Ph 4-n-C₆F₁₃SO₂—Ph H H H CH₃ H O 1 119 4-Cl—Ph 4-CF₃SO₂NH—Ph HH H CH₃ H O 1 120 4-Cl—Ph 4-(5-CF₃-2-Pyr)O H H H CH₃ H O 1 —Ph 1214-Cl—Ph 2,4-Cl₂—Ph H H H CH₃ H O 1 122 4-Cl—Ph 3,4-Cl₂—Ph H H H CH₃ H O1 123 4-Cl—Ph 3-Cl-4-F—Ph H H H CH₃ H O 1 124 4-Cl—Ph 3-CF₃—4-NO₂—Ph H HH CH₃ H O 1 125 4-Cl—Ph 3,5-(CH₃)₂-Ph H H H CH₃ H O 1 126 4-Cl—Ph2,3,4,5,6-F₆—Ph H H H CH₃ H O 1 127 4-Cl—Ph 4-(Cl₂C═CH— H H H CH₃ H O 1CH₂O)—Ph 128 4-Cl—Ph 4-(Cl₂C═CH— H H H CH₃ H O 1 CH₂S)—Ph 129 4-Cl—Ph4-(Cl₂C═CH— H H H CH₃ H O 1 CH₂SO₂)—Ph 130 4-Cl—Ph 2,6-Cl₂-4-(Cl₂ H H HCH₃ H O 1 —C═CHCH₂O)—Ph 131 4-Cl—Ph 4-CN—Ph H H H CH₃ H O 1 132 4-Cl—Ph4-NO₂-Ph H H H CH₃ H O 1 133 4-Cl—Ph 4-(Ph—C═C)Ph H H H CH₃ H O 1 1344-Cl—Ph 2-Naph H H H CH₃ H O 1 135 4-Cl—Ph 6-Cl-2-Naph H H H CH₃ H O 1136 4-Cl—Ph 6-CF₃-2-Naph H H H CH₃ H O 1 137 4-Cl—Ph 5-Cl-2-Pyr H H HCH₃ H O 1 138 4-Cl—Ph 6-Cl-3-Pyr H H H CH₃ H O 1 139 4-Cl—Ph 5-NO₂-2-PyrH H H CH₃ H O 1 140 4-Cl—Ph 5-CN-2-Pyr H H H CH₃ H O 1 141 4-F—Ph4-Cl—Ph H H H CH₃ H O 1 142 4-F—Ph 4-Cl—Ph H H H CH₃ H N—CH₃ 1 1434-F—Ph 4-F—Ph H H H CH₃ H O 1 144 4-F—Ph 4-I—Ph H H H CH₃ H O 1 1454-F—Ph 4-i-C₃H₇—Ph H H H CH₃ H O 1 146 4-F—Ph 4-CF₃O—Ph H H H CH₃ H O 1147 4-F—Ph 4-CF₃—Ph H H H CH₃ H O 1 148 4-F—Ph 4-CN—Ph H H H CH₃ H O 1149 4-F—Ph 4-NO₂-Ph H H H CH₃ H O 1 150 4-F—Ph 3-Cl-4-F—Ph H H H CH₃ H O1 151 4-F—Ph 2,3,4,5,6- H H H CH₃ H O 1 F₅—Ph 152 4-F—Ph 6-Cl-2-Pyr H HH CH₃ H O 1 153 4-Br—Ph 4-Cl—Ph H H H CH₃ H O 1 154 2-I—Ph 4-CF₃—Ph H HH CH₃ H O 1 155 4-I—Ph 4-Cl—Ph H H H CH₃ H O 1 156 4-I—Ph 4-I—Ph H H HCH₃ H O 1 157 4-I—Ph 4-CF₃—Ph H H H CH₃ H O 1 158 2-CH₃—Ph 3,5-(CH₃)₂- HH H CH₃ H O 1 Ph 159 2-CH₃—Ph 4-CF₃—Ph H H H CH₃ H O 1 160 3-CH₃—Ph3,5-(CH₃)₂- H H H CH₃ H O 1 Ph 161 4-CH₃—Ph 3,5-(CH₃)₂- H H H CH₃ H O 1Ph 162 2-CH₃O—Ph 3,5-(CH₃)₂- H H H CH₃ H O 1 Ph 163 3-CF₃—Ph 4-Cl—Ph H HH CH₃ H O 1 164 4-CH₃O—Ph 3,5-(CH₃)₂ H H H CH₃ H O 1 165 4-CH₃O—Ph4-Cl—Ph H H H CH₃ H O 1 166 4-CH₃O—Ph 4-Cl—Ph H H H CH₃ CH₃ O 1 1674-CH₃O—Ph 4-Cl—Ph H H H CH₃ n-C₃H₇ O 1 168 4-CH₃O—Ph 4-Cl—Ph H H H CH₃n-C₃H₇ O 1 169 4-CH₃O—Ph 4-Cl—Ph H H H CH₃ n-C₄H₉ O 1 170 4-CH₃O—Ph4-Cl—Ph H H H CH₃ H O 4 171 4-CH₃O—Ph 4-Cl—Ph H H H C₂H₅ H O 1 1724-CH₃O—Ph 4-Cl—Ph H H H n-C₃H₇ H O 1 173 4-CH₃O—Ph 4-Cl—Ph H H H i-C₃H₇H O 1 174 4-CH₃O—Ph 4-Cl—Ph H H H c-C₃H₅ H O 1 175 4-CH₃O—Ph 4-Cl—Ph H HH t-C₄H₉ H O 1 176 4-CH₃O—Ph 4-Cl—Ph H H H (CH₂)₄ O 1 177 4-CF₃O—Ph4-Cl—Ph H H H CH₃ H O 1 178 4-CHF₂O—Ph 4-Cl—Ph H H H CH₃ H O 1 1794-CF₃SO₂O— 4-Cl—Ph H H H CH₃ H O 1 Ph 180 4-CHF₂S—Ph 4-Cl—Ph H H H CH₃ HO 1 181 4-CHF₂SO₂—Ph 4-Cl—Ph H H H CH₃ H O 1 182 4-CF₃S—Ph 4-Cl—Ph H H HCH₃ H O 1 183 4-CF₃SO₂—Ph 4-Cl—Ph H H H CH₃ H O 1 184 4-n-C₃F₇—Ph4-Cl—Ph H H H CH₃ H O 1 185 4-CF₃SO₂NH— 4-Cl—Ph H H H CH₃ H O 1 Ph 1864-CF₃—Ph 2-Cl—Ph H H H CH₃ H O 1 187 4-CF₃—Ph 4-Cl—Ph H H H CH₃ H O 1188 4-CF₃—Ph 4-F—Ph H H H CH₃ H O 1 189 4-CF₃—Ph 4-I—Ph H H H CH₃ H O 1190 4-CF₃—Ph 2,4-Cl₂—Ph H H H CH₃ H O 1 191 4-CF₃—Ph 2,4-F₂—Ph H H H CH₃H O 1 192 4-CF₃—Ph 2,6-F₂—Ph H H H CH₃ H O 1 193 4-CF₃—Ph 4-I-2-CH₃—Ph HH H CH₃ H O 1 194 4-CF₃—Ph 4-CH₃—Ph H H H CH₃ H O 1 195 4-CF₃—Ph4-CF₃—Ph H H H CH₃ H O 1 196 4-CF₃—Ph 4-C₂F₃—Ph H H H CH₃ H O 1 1974-CF₃—Ph 4-n-C₃F₇—Ph H H H CH₃ H O 1 198 4-CF₃—Ph 4-i-C₃F₇—Ph H H H CH₃H O 1 199 4-CF₃—Ph 4-(PhO)—Ph H H H CH₃ H O 1 200 4-CF₃—Ph 4-CF₃O—Ph H HH CH₃ H O 1 201 4-CF₃—Ph 4-CHF₂O—Ph H H H CH₃ H O 1 202 4-CF₃—Ph4-CF₃SO₂O—Ph H H H CH₃ H O 1 203 4-CF₃—Ph 4-CF₃S—Ph H H H CH₃ H O 1 2044-CF₃—Ph 4-CF₃SO₂—Ph H H H CH₃ H O 1 205 4-CF₃—Ph 4-CHF₂S—Ph H H H CH₃ HO 1 206 4-CF₃—Ph 4-CHF₂SO₂—Ph H H H CH₃ H O 1 207 4-CF₃—Ph 4-n-C₃F₇S—PhH H H CH₃ H O 1 208 4-CF₃—Ph 4-i-C₃F₇S—Ph H H H CH₃ H O 1 209 4-CF₃—Ph4-n-C₃F₇SO₂—Ph H H H CH₃ H O 1 210 4-CF₃—Ph 4-n-C₆F₁₃S—Ph H H H CH₃ H O1 211 4-CF₃—Ph 4-n-C₆F₁₃SO₂- H H H CH₃ H O 1 Ph 212 4-CF₃—Ph4-CF₃SO₂NH—Ph H H H CH₃ H O 1 213 4-CF₃—Ph 4-COOCH₃—Ph H H H CH₃ H O 1214 4-CF₃—Ph 2-(Cl₂C═CH— H H H CH₃ H O 1 CH₂O)—Ph 215 4-CF₃—Ph4-(Cl₂C═CH— H H H CH₃ H O 1 CH₂S)—Ph 216 4-CF₃—Ph 4-(Cl₂C═CH— H H H CH₃H O 1 CH₂SO₂)—Ph 217 4-CF₃—Ph 2,6-Cl₂-4-(Cl₂- H H H CH₃ H O 1C═CHCH₂O)—Ph 218 4-CF₃—Ph— 4-(t-C₄H₉C≡C) H H H CH₃ H O 1 Ph 2194-CF₃—Ph— 4-(Ph—C≡C) H H H CH₃ H O 1 Ph 220 4-C₂F₅—Ph 4-Cl—Ph H H H CH₃H O 1 221 4-C₂F₅—Ph 4-CF₃—Ph H H H CH₃ H O 1 222 4-C₂F₅—Ph 4-i-C₃F₇—Ph HH H CH₃ H O 1 223 4-n-C₃F₇—Ph 4-Cl—Ph H H H CH₃ H O 1 224 4-n-C₃F₇—Ph4-CF₃—Ph H H H CH₃ H O 1 225 4-n-C₃F₇—Ph 4-i-C₃F₇—Ph H H H CH₃ H O 1 2264-i-C₃F₇—Ph 4-Cl—Ph H H H CH₃ H O 1 227 4-i-C₃F₇—Ph 4-CF₃—Ph H H H CH₃ HO 1 228 4-i-C₃F₇—Ph 4-i-C₃F₇—Ph H H H CH₃ H O 1 229 4-NO₂—Ph 4-F—Ph H HH CH₃ H O 1 230 4-Ph—Ph 4-Cl—Ph H H H CH₃ H O 1 231 2,4-Cl₂—Ph 4-Cl—Ph HH H CH₃ H O 1 232 2,4-Cl₂—Ph 4-Cl—Ph CH₃O H H CH₃ H O 1 233 2,4-Cl₂—Ph4-CF₃—Ph H H H CH₃ H O 1 234 2,6-Cl₂—Ph 4-Cl—Ph H H H CH₃ H O 1 2352,6-F₂—Ph 4-Cl—Ph H H H CH₃ H O 1 236 2,6-F₂—Ph 4-CF₃—Ph H H H CH₃ H O 1237 3,4-F₂—Ph 4-F—Ph H H H CH₃ H O 1 238 3,4-F₂—Ph 4-CF₃—Ph H H H CH₃ HO 1 239 2,3-(CH₃)₂-Ph 3,5-(CH₃)₂- H H H CH₃ H O 1 Ph 240 3,5-(CH₃)₂-Ph4-CH₃—Ph H H H CH₃ H O 1 241 3,5-(CH₃)₂-Ph 4-OCH₃—Ph H H H CH₃ H O 1 2423,5-(CH₃)₂-Ph 2,3-(CH₃)₂ H H H CH₃ H O 1 -Ph 243 3,5-(CF₃)₂-Ph 4-CF₃—PhH H H CH₃ H O 1 244 2,4,6-(CH₃)₃-Ph 4-Cl—Ph H H H CH₃ H O 1 2452,3,4,5,6-F₅—Ph 4-F—Ph H H H CH₃ H O 1 246 5-Cl-2-Pyr 4-Cl—Ph H H H CH₃H O 1 247 5-Cl-2-Pyr 4-CF₃—Ph H H H CH₃ H O 1 248 5-Cl-2-Pyr 5-Cl-2-PyrH H H CH₃ H O 1 249 5-Cl-2-Pyr 5-CF₃-2- H H H CH₃ H O 1 Pyr 2506-Cl-3-Pyr 4-Cl—Ph H H H CH₃ H O 1 251 6-Cl-3-Pyr 4-CF₃—Ph H H H CH₃ H O1 252 5-CF₃-2-Pyr 4-Cl—Ph H H H CH₃ H O 1 253 5-CF₃-2-Pyr 4-CF₃—Ph H H HCH₃ H O 1 254 5-CF₃-2-Pyr 4-Cl-2-Pyr H H H CH₃ H O 1 255 5-CF₃-2-Pyr4-CF₃-2- H H H CH₃ H O 1 Pyr 256 6-CF₃-3-Pyr 4-Cl—Ph H H H CH₃ H O 1 2576-CF₃-3-Pyr 4-CF₃—Ph H H H CH₃ H O 1 258 5-CN-2-Pyr 4-Cl—Ph H H H CH₃ HO 1 259 5-NO₂-2-Pyr 4-Cl—Ph H H H CH₃ H O 1 260 5-CF₃O-2-Pyr 4-Cl—Ph H HH CH₃ H O 1 261 5-CF₃O-2-Pyr 4-CF₃—Ph H H H CH₃ H O 1 262 5-CF₃S-2-Pyr4-Cl—Ph H H H CH₃ H O 1 263 5-CF₃S-2-Pyr 4-CF₃—Ph H H H CH₃ H G 1 2645-CF₃SO₂-2-Pyr 4-Cl—Ph H H H CH₃ H O 1 265 5-CF₃SO₂-2-Pyr 4-CF₃—Ph H H HCH₃ H O 1 266 3,5-Cl₂-2-Pyr 4-Cl—Ph H H H CH₃ H C 1 267 3,5-Cl₂-2-Pyr4-CF₃—Ph H H H CH₃ H O 1 268 5-CF₃-3-Cl-2-Pyr 4-Cl—Ph H H H CH₃ H O 1269 5-CF₃-3-Cl-2-Pyr 4-CF₃—Ph H H H CH₃ H O 1 270 2-Naph 4-Cl—Ph H H HCH₃ H O 1 271 6-Cl-2-Naph 4-Cl—Ph H H H CH₃ H O 1 272 6-Cl-2-Naph4-CF₃—Ph H H H CH₃ H O 1 273 6-CF₃-2-Naph 4-Cl—Ph H H H CH₃ H O 1 2746-CF₃-2-Naph 4-CF₃—Ph H H H CH₃ H O 1 275 6-CF₃O-2-Naph 4-Cl—Ph H H HCH₃ H O 1 276 6-CF₃S-2-Naph 4-Cl—Ph H H H CH₃ H O 1 277 6-CF₃SO₂-2-Naph4-Cl—Ph H H H CH₃ H O 1 278 4-CF₃—Ph 4-Cl—Ph H H H CH₃ H O 1 b═1 2794-Cl—Ph 4-Cl—Ph H H H CH₃ H O 1 b═1 280 4-Cl—Ph Ph H H H CH₃ H O 1R⁷═CH₃, b═1 281 4-CF₃—Ph Ph H H H CH₃ H O 1 R⁷═CH₃, b═1 282 4-CF₃O—Ph4-CF₃—Ph H H H CH₃ H O 1 283 2-F-4-Cl—Ph 4-CF₃—Ph H H H CH₃ H O 1 2842-Cl-4-F—Ph 4-CF₃—Ph H H H CH₃ H O 1 285 2,4-F₂—Ph 4-CF₃—Ph H H H CH₃ HO 1 286 4-(PhC═C)Ph 4-Cl—Ph H H H CH₃ H O 1

TABLE 2 (R⁶═R⁷═R⁸═H, b═O) No. Ar¹ Ar² (Q)_(d) R³ R⁴ R⁵ W a 287 Ph4-Cl—Ph CH═CH H CH₃ H O 1 288 Ph 4-Cl—Ph C═C H CH₃ H O 1 289 Ph4-CF₃O—Ph C═C H CH₃ H O 1 290 4-Cl—Ph 4-Cl—Ph CH═CH H CH₃ H O 1 2914-Cl—Ph 4-CF₃—Ph C═C H CH₃ H O 1

TABLE 2 (R⁶═R⁷═R⁸═H, b═O) No. Ar¹ Ar² (Q)_(d) R³ R⁴ R⁵ W a 287 Ph4-Cl—Ph CH═CH H CH₃ H O 1 288 Ph 4-Cl—Ph C═C H CH₃ H O 1 289 Ph4-CF₃O—Ph C═C H CH₃ H O 1 290 4-Cl—Ph 4-Cl—Ph CH═CH H CH₃ H O 1 2914-Cl—Ph 4-CF₃—Ph C═C H CH₃ H O 1

In table 1, Table 2 and Table 3, Ph represents phenyl group, Pyrrepresents pyridyl group, Naph represents naphtyl group and c-representsalicyclic hydrocarbon.

Table 4 shows physical properties of the compound listed in the Table 1,Table 2 and Table 3.

TABLE 4 Physical properties (melting point, refractive index, No.NMR(CDCl₃/TMS), δ value (ppm))  1 m.p. 101° C.  2 m.p. 152° C.  3 m.p.121° C.  9 nD 1.542(21° C.)  10 paste NMR: 1.65(s.3H), 1.51-1.72(m.4H),1.80-2.12(m.4H), 3.69(s.2H), 3.95-4.03(m.2H), 5.59(br.1H),6.8-6.9(m.2H), 7.1-7.40(m.6H).  11 paste NMR: 1.74(s.3H), 2.06(m.2H),3.61(m.2H), 3.55-3.80(m.2H), 4.28(m.2H), 7.06(br.1H), 7.12(d.2H),7.18-7.24(m.2H), 7.25-7.40(m.4H).  12 m.p. 127-133° C.  13 m.p. 138-139°C.  14 m.p. 98-99° C. (Rf = H)  15 paste (Rf = L) NMR: 1.32(d.3H),1.75(s.3H), 3.72(s.2H), 4.60-4.70(m.1H), 5.97(br.1H), 6.76(d.2H),7.20-7.42(m.6H).  16 paste (Rf = L) NMR: 0.83(t.3H), 1.20-2.00(m.4H),3.66(s.2H), 4.82(br.1H), 5.87(br.1H), 6.86(d.2H), 7.15-7.30(m.6H).  17paste (Rf = H) NMR: 0.89(t.3H), 1.20-2.00(m.4H), 3.40-3.57(m.2H),5.02(br.1H), 5.70(br.1H), 6.73(d.2H), 7.05-7.30(m.6H).  18 m.p. 125-128°C. (Rf = H)  19 paste (Rf = L) NMR: 0.81(t.3H), 1.10-1.80(m.6H),3.67(s.2H), 4.75-4.82(m.1H), 5.79(br.1H), 6.85(d.2H), 7.18-7.40(m.6H). 20 m.p. 97° C.  21 m.p. 131° C.  22 m.p. 107-110° C.  23 m.p. 123-126°C.  24 m.p. 125-126° C.  25 paste NMR: 1.08(s.9H), 3.68-3.82(m.2H),4.36-4.47(m.2H), 5.69(br.1H), 6.75(d.2H), 7.18-7.46(m.6H).  26 m.p.78-84° C.  27 paste NMR: 1.94(s.3H), 3.20(s.3H), 3.83(m.2H), 4.46(s.2H),6.82(d.2H), 7.12-7.30(m.5H), 7.37(d.1H).  28 m.p. 110-112° C.  29 m.p.118-120° C.  30 m.p. 72-74° C.  41 m.p. 132-133° C.  42 m.p. 116-117° C. 44 m.p. 134-143° C. (Rf = H)  45 paste (Rf = L) NMR: 1.31(d.3H),1.74(s.3H), 3.54(s.2H), 4.62-4.70(m.1H), 6.12(br.1H), 6.76(d.2H),7.06-7.30(m.6H).  46 paste (Rf = H) NMR: 0.92(t.3H), 1.20-2.00(m.4H),3.29(s.2H), 5.02-5.12(s.1H), 5.45(m.1H), 6.75(d.2H), 7.13-7.26(m.6H). 47 paste (Rf = L) NMR: 0.85(t.3H), 1.20-2.00(m.4H), 3.49(s.2H),4.78-4.81(m.1H), 5.81(br.1H), 6.84(d.2H), 7.15-7.30(m.6H).  48 m.p.134-136° C.  49 m.p. 103-104° C.  50 paste NMR: 1.65(s.3H),1.50-2.10(m.6H), 3.54(s.2H), 3.88-3.93(s.2H), 5.52(br.1H), 6.79(d.2H),7.10-7.30(m.6H).  51 m.p. 96-99° C.  52 m.p. 121-122° C.  53 m.p.121-124° C.  54 paste NMR: 1.07(s.9H), 3.52-3.66(m.2H), 4.33-4.52(m.2H),5.55(br.1H), 6.78(d.2H), 7.10-7.33(m.6H).  55 paste NMR:1.20-2.00(m.8H), 3.49(s)/3.52(s)(2H), 4.35(br)/4.85(br)(1H),5.62(br)/5.95(br)(1H), 6.70-6.80(m.2H), 7.00-7.30(m.6H).  56 m.p.113-114° C.  57 m.p. 132-135° C.  58 m.p. 142° C.  59 m.p. 169° C.  60m.p. 126-127° C.  61 paste NMR: 1.64(s.3H), 1.52-2.15(m.8H), 3.53(s.3H),3.95-4.03(m.2H), 5.59(br.1H), 6.86-6.95(m.2H), 7.12-7.40(m.6H).  62 m.p.126-127° C.  63 m.p. 122-128° C.  64 m.p. 152° C.  65 m.p. 87-89° C.  66m.p. 95° C.  67 m.p. 153° C.  68 paste NMR: 1.64(s.3H), 1.50-2.10(m.6H),3.54(s.2H), 3.87-3.93(m.2H), 5.47(br.1H), 6.80(d.2H), 7.15-7.40(m.6H). 69 m.p. 124-141° C.  70 paste NMR: 0.85(t)/0.92(t)(3H),1.20-2.00(m.4H), 3.21-3.36(m)/3.49(s)(2H),4.74-4.80(br)/5.04-5.12(br)(1H), 5.41(br)/5.76(br)(1H), 6.70-7.30(m.8H). 71 m.p. 124-130° C. (Rf = H)  73 m.p. 126-127° C.  74 m.p. 104-105° C. 75 m.p. 140° C.  76 m.p. 142° C.  77 paste NMR: 1.07(s.9H),3.52-3.66(m.2H), 4.34-4.50(m.2H), 5.57(br.1H), 6.75(d.2H),7.12-7.37(m.6H).  79 paste NMR: 1.20-2.10(m.8H), 3.48(s)/3.50(s)(2H),4.32(br)/4.84(br)(1H), 5.60(br)/5.90(br)(1H), 6.67-6.75(m.2H),7.00-7.30(m.6H).  80 paste NMR: 1.91(s.3H), 3.11(s.3H), 3.70(s.2H),4.39-4.51(m.2H), 6.78(d.2H), 7.09((d.2H), 7.22-7.26(m.4H).  81 m.p.83-84° C.  82 m.p. 57-63° C.  83 m.p. 114-117° C.  84 m.p. 105-108° C. 85 m.p. 148-149° C. (Rf = H)  86 m.p. 152-154° C. (Rf = L)  88 m.p.145-146° C.  89 m.p. 123° C.  90 m.p. 135-137° C.  91 m.p. 96-97° C.  92m.p. 160-161° C.  94 m.p. 127-130° C.  95 m.p. 132-133° C.  96 m.p.120-121° C.  97 m.p. 96-100° C.  99 m.p. 114-115° C. 100 m.p. 126-127°C. 102 m.p. 162° C. 103 m.p. 159-163° C. 105 m.p. 130° C. 108 m.p.85-86° C. 109 paste NMR: 1.80(s.3H), 3.03(s.3H), 3.58(s.2H),4.32(dd.2H), 5.88(br.1H), 6.96(d.2H), 7.18(s.2H), 7.32(d.2H),7.86(d.2H). 114 m.p. 91-92° C. 116 paste NMR: 1.81(s.3H), 3.59(s.2H),4.36-4.45(m.2H), 5.68(br.1H), 7.03-7.10(m.2H), 7.18(d.2H), 7.33(d.2H),7.76(d.1H), 7.99(d.1H). 117 m.p. 102-104° C. 118 paste NMR: 1.81(s.3H),3.59(s.2H), 4.30-4.45(m.2H), 5.66(br.1H), 7.04-7.10(m.2H), 7.17(d.2H),7.33(d.2H), 7.75(d.1H), 7.99(d.1H). 120 m.p. 160-161° C. 121 m.p. 88-90°C. 122 m.p. 125-126° C. 123 m.p. 93-94° C. 124 m.p. 141-142° C. 125 m.p.175-176° C. 126 nD 1.511(26° C.) 125 m.p. 88-89° C. 128 m.p. 87-89° C.129 paste NMR: 1.81(s.3H), 3.59(s.2H), 3.93(d.2H), 4.35(dd.2H),5.80(br.1H), 5.98(t.1H), 6.98(d.2H), 7.19(d.2H), 7.33(d.2H), 7.82(d.2H).130 m.p. 127-128° C. 133 m.p. 156-158° C. 134 m.p. 146-147° C. 141 m.p.159-160° C. 142 m.p. 156-157° C. 143 m.p. 128-129° C. 144 m.p. 144° C.145 m.p. 137-139° C. 146 m.p. 107-109° C. 147 m.p. 112-113° C. 148 m.p.138-140° C. 149 m.p. 108-110° C. 150 m.p. 128-129° C. 151 m.p. 108-110°C. 152 m.p. 136° C. 153 m.p. 146° C. 154 m.p. 146-147° C. 156 m.p.142-143° C. 157 m.p. 98-99° C. 158 m.p. 123-124° C. 160 m.p. 117-118° C.161 m.p. 110-112° C. 163 nD 1.521(21° C.) 164 m.p. 126-127° C. 165 m.p.115° C. 166 m.p. 129-131° C. 167 paste (Rf = H) NMR: 0.91(t.3H),1.20-1.90(m.4H), 3.18-3.38(m.2H), 3.78(s.3H), 5.04-5.12(m.1H),5.39(br.1H), 6.70-6.82(m.6H), 7.20(d.2H). 168 paste (Rf = L) NMR:0.84(t.3H), 1.20-1.90(m.4H), 3.41-3.55(m.2H), 3.79(s.3H),4.72-4.80(m.1H), 5.72(br.1H), 6.78-6.85(m.4H), 7.05(d.2H), 7.24(d.2H).169 m.p. 121-126° C. (Rf = H) 170 paste NMR: 1.61(s.3H),1.45-2.10(m.6H), 3.52(s.2H), 3.78(s.3H), 3.85-3.93(m.2H), 5.44(br.1H),6.78(d.1H), 6.87(d.2H), 7.15(d.2H), 7.28(d.2H). 171 m.p. 104-107° C. 172paste NMR: 0.95(t.3H), 1.35-1.55(m.2H), 1.95-2.05(m.2H), 3.53(s.2H),3.80(s.3H), 4.19-4.33(m.2H), 5.63(br.1H), 6.74(d.2H), 6.87(d.2H),7.11(d.2H), 7.23(d.2H). 173 m.p. 114-117° C. 174 m.p. 119-122° C. 175paste NMR: 1.03(s.9H), 3.49-3.64(m.2H), 3.81(s.3H), 4.32-4.50(m.2H),5.58(br.1H), 6.77(d.2H), 6.91(d.2H), 7.13(d.2H), 7.24(d.2H). 176 pasteNMR: 1.20-2.10(m.8H), 3.43-3.55(m.2H), 3.73(s)/3.87(s)(3H),4.26(br)/4.80(br)(1H), 5.61(br)/5.86(br)(1H), 6.65-7.25(m.8H). 184 m.p.87-88° C. 186 m.p. 130° C. 187 m.p. 119° C. 188 m.p. 128-130° C. 189m.p. 145-147° C. 190 m.p. 80-81° C. 191 m.p. 88-90° C. 192 m.p. 112-113°C. 193 m.p. 108-109° C. 195 m.p. 95-96° C. 196 m.p. 105-111° C. 197 m.p.82-85° C. 199 m.p. 135-136° C. 200 m.p. 85-87° C. 207 m.p. 59-60° C. 209paste NMR: 1.83(s.3H), 3.67(s.3H), 4.30-4.50(m.2H), 5.82(br.1H),7.03-7.05(m.2H), 7.37(d.2H), 7.61(d.2H), 7.74(d.1H), 7.98(d.1H) 210 m.p.90-91° C. 211 paste NMR: 1.83(s.3H), 3.68(s.2H), 4.30-4.46(m.2H),5.73(br.1H), 7.03-7.10(m.2H), 7.38(d.2H), 7.61(d.2H), 7.75(d.1H),7.98(d.1H). 213 m.p. 103-105° C. 216 m.p. 87-88° C. 218 m.p. 159-161° C.219 m.p. 177-178° C. 220 m.p. 140-143° C. 221 m.p. 133-137° C. 223 m.p.88-89° C. 224 m.p. 86-88° C. 229 nD 1.554(26° C.) 230 m.p. 131-132° C.231 m.p. 100° C. 232 nD 1.543(21° C.) 233 m.p. 123-124° C. 234 m.p. 141°C. 235 m.p. 130-131° C. 236 m.p. 154-155° C. 237 m.p. 94° C. 238 m.p.85° C. 243 m.p. 104-106° C. 244 m.p. 136° C. 245 m.p. 87° C. 253 m.p.97-99° C. 269 m.p. 137-139° C. 270 m.p. 138° C. 278 m.p. 71-73° C. 279m.p. 103-106° C. 280 m.p. 106-108° C. 281 m.p. 114-117° C. 282 m.p.121-125° C. 283 m.p. 105-106° C. 284 m.p. 141-143° C. 285 m.p. 115-120°C. 286 m.p. 162-164° C. 287 m.p. 140-142° C. 288 paste NMR: 1.89(s.3H),4.27(s.2H), 6.52(br.1H), 7.26(d.2H), 7.30-7.60(m.5H). 289 paste NMR:1.91(s.3H), 4.31(s.2H), 6.28(br.1H), 6.96(d.2H), 7.35-7.60(m.5H). 290m.p. 163-164° C. 291 paste NMR: 1.92(s.3H), 4.37(s.2H), 6.33(br.1H),7.02(d.2H), 7.35(d.2H), 7.47(d.2H), 7.59(d.2H), 292 m.p. 135-140° C. 293m.p. 135-136° C. 294 m.p. 115° C. 295 m.p. 128-130° C. 296 m.p. 118-119°C. 297 m.p. 134-140° C. 298 m.p. 125-135° C. 299 paste NMR:1.40-2.30(m.8H), 4.62/4.99(br.s.1H), 6.38/6.62(br.s.1H),6.99-6.97(m.2H), 7.16-7.30(m.2H), 7.62-7.82(m.4H) 300 paste NMR:1.50-2.35(m.8H), 1.84(s.3H), 4.12(q.2H), 6.31(br.s.1H), 6.92(d.2H),7.21(dd.1H), 7.34(dd.1H), 7.66(d.2H), 7.85(d.2H) 301 m.p. 135-136° C.302 m.p. 217-218° C. 303 m.p. 195-198° C 304 m.p. 129-130° C. 305 m.p.106-108° C. 306 m.p. 132-136° C. 307 m.p. 92° C. 308 m.p. 72-77° C. 309m.p. 135-137° C. 310 m.p. 120-122° C. 311 m.p. 155-160° C. 312 m.p.96-97° C. 313 m.p. 127-129° C. 314 m.p. 127-128° C. 315 m.p. 161-166° C.316 paste NMR: 1.98(s.3H), 4.45(q.2H), 6.65(br.s.1H), 7.03(d.2H),7.58(d.2H), 7.76(d.2H), 7.88(d.2H) 317 paste NMR: 1.98(s.3H),4.47(s.2H), 6.33(br.s.1H), 7.01(d.1H), 7.32(m.4H), 7.57(d.2H) 318 pasteNMR: 1.97(s.3H), 4.44(q.2H), 6.56(br.s.1H), 7.02(d.2H), 7.53(m.1H),7.61(d.2H), 7.63(s.2H) 319 m.p. 122-123° C. 320 m.p. 149-154° C. 321m.p. 144-145° C. 322 m.p. 205-208° C. 323 m.p. 142-144° C. 324 m.p.147-148° C. 325 m.p. 130-132° C. 326 m.p. 98-100° C. 327 m.p. 118-121°C. 328 m.p. 140-141° C. 329 m.p. 137-140° C. 330 m.p. 166-168° C. 331m.p. 187-190° C. 332 m.p. 85-88° C. 333 m.p. 127-128° C. 334 m.p.171-173° C. 335 m.p. 158-159° C. 336 m.p. 150-154° C. 337 m.p. 137-140°C. 338 m.p. 219-222° C. 339 m.p. 126-130° C. 340 m.p. 133-134° C. 341paste NMR: 1.99(s.3H), 2.50(s.3H), 4.41(d.1H), 4.49(d.1H), 7.03(d.2H),7.25(d.2H), 7.30(br.s.1H), 7.59(d.2H), 8.18(d.1H) 342 m.p. 119-123° C.343 m.p. 249-251° C. 344 m.p. 184-187° C. 345 m.p. 254-257° C. 346 m.p.170-173° C. 347 m.p. 111-114° C. 348 paste NMR: 1.97(s.3H), 4.40(d.1H),4.47(d.1H), 6.65(br.s.1H), 7.03(d.2H), 7.19-7.23(m.1H), 7.59(d.2H),7.62(t.1H), 7.80-7.91(m.1H), 8.55-8.57(m.1H) 349 paste NMR: 1.94(s.3H),4.41(dd.2H), 6.71(br.s.1H), 6.93(d.1H), 7.00(d.2H), 7.45(t.2H),7.55(d.2H), 8.11-8.14(m.1H), 8.56(d.1H) 350 m.p. 118-119° C. 351 m.p.161-163° C. 352 m.p. 132-139° C. 353 m.p. 149-151° C. 354 paste NMR:1.22-1.29(m.6H), 2.76(m.1H), 4.60(q.2H), 6.70(br.s.1H), 6.99(d.2H),7.34(m.1H), 7.43(m.1H), 7.48(d.2H), 7.70(d.2H) 355 paste NMR:1.20-1.32(m.6H), 2.81(m.1H), 4.60(q.2H), 6.43(br.s.1H), 6.98(d.2H),7.55(d.2H), 7.76-7.86(m.4H), 7.70(d.2H) 356 paste NMR: 1.52-1.57(m.3H),1.91/1.93(s.3H), 5.03/5.26(q.2H), 6.76/6.96(br.s.1H), 6.98-7.10(m.2H),7.26-7.79(m.5H) 357 m.p. 210-213° C. (Rf = H) 358 m.p. 206-208° C. (Rf =L) 359 m.p. 90-91° C. 360 m.p. 137-140° C. 361 m.p. 132° C. 362 pasteNMR: 1.99(s.3H), 4.43(d.2H), 4.49(d.1H), 7.04(d.2H), 7.57(d.2H),7.89(d.1H), 8.25(br.s.1H), 8.41(d.1H) 363 paste NMR: 1.99(s.3H),2.61(s.3H), 4.46(s.2H), 7.02-7.09(m.4H), 7.58(d.2H), 7.92-7.96(m.1H),8.53-8.55(m.1H) 364 m.p. 200-202° C. 365 m.p. 137-142° C. 366 m.p.130-133° C. 367 m.p. 138-140° C. 368 m.p. 141-142° C. 369 m.p. 138-139°C.

In Table 3 or 4, Rf-H or Rf-L indicates stereoisomers; Rf-H indicates anisomer having a high Rf values from among the stereoisomers, and Rf-Hindicates isomers having a low Rf value.

Hereafter, typical examples, formulation examples, and test examples ofthe present invention.

EXAMPLES Example 1

Production of Compound No. 63

4-Chlorophenol (2.56 g), bromoacetaldehyde dimethylacetal acetal (3.4g), anhydrous pottasium carbonate (2.76 g) and a catalytic amount ofsodium iodide were added to DMF (dimethylformamide)(20 ml) and heatedunder reflux for 3 hours. Water was added to the reaction mixture, whichwas then extracted with ethyl acetate and the organic layer was driedover anhydrous sodium sulfate, and the solvent was distilled off theresidue was purified by silica gel column chromatography (ethylacetate-hexane) to obtain 4-chlorophenoxyacetaldehyde dimethylacetal(2.37 g).

4-Chlorophenoxyacetaldehyde dimethylacetal (1.0 g) was dissolved inacetone (10 ml), to which 2N hydrochloric acid (1.0 g) was added, andthe mixture was heated under reflux for 8 hours. After the reactionmixture was concentrated, water was added and the mixture was extractedwith ethyl acetate. The extracts were dried over anhydrous sodiumsulfate. The solvent was distilled off to obtain4-chlorophenoxyacetaldehyde as a crude product.

Crude 4-chlorophenoxyacetaldehyde (0.5 g), sodium cyanide (0.17 g) andammonium chloride (0.27 g) were added into 28% ammonia water (20 ml) andstirred for 2 days. To the reaction solution was added ethyl acetate andthe mixture was washed with water and dried over anhydrous sodiumsulfate and the solvent was distilled off. The resulting oil wasdissolved in THF (tetrahydrofuran)(5 ml) and added with4-chlorophenylacetyl chloride (0.38 g) and triethylamine (0.22 g). Themixture was stirred at room temperature for 6 hours. Water was added tothe reaction mixture, which was extracted with ethyl acetate and theextracts were dried over anhydrous sodium sulfate and the solvent wasdistilled off. The residue was purified by silica gel columnchromatography (ethyl acetate-hexane) to obtain the intended compound(0.21 g; yield 24%; m.p. 122-128° C.).

Example 2

Production of Compound No. 64

4-Chlorophenol (10 g), chloroacetone (10.8 g), anhydrous potassiumcarbonate (12.9 g) and potassium iodide (1.3 g) were added to acetone(100 ml) and heated under reflux for 6 hours. The reaction mixture wasfiltered and the filtrate was concentrated to obtain4-chlorophenoxyacetone (14 g).

4-Chlorophenoxyacetone (6.0 g), sodium cyanide (1.91 g) and ammoniumchloride (2.6 g) were added into 28% ammonia water (20 ml) and stirredvigorously for twenty-four hours. To the reaction mixture was addedethyl acetate and the mixture was washed with water and dried overanhydrous sodium sulfate and the solvent was distilled off to obtain2-amino-2-methyl-3-(4-chlorophenoxy)propanenitrile (6.5 g).

4-Chlorophenylacetic acid (0.4 g) was added to thionyl chloride (1 ml)and heated under reflux for 1 hour and excess thionyl chloride wasdistilled off under reduced pressure. The resulting acid chloride wasadded to THF solution (5 ml) in which2-amino-2-methyl-3-(4-chlorophenoxy)propanenitrile (0.49 g) andtriethylamine (0.26 g) were dissolved under ice cooling and stirred atroom temperature for 3 hours. To the reaction mixture was added waterand the mixture was extracted with ethyl acetate. The extracts weredried over anhydrous sodium sulfate and the solvent was distilled off.The solid residue was washed with hexane-ether to obtain the intendedcompound (0.56 g; yield 66%; m.p. 152° C.).

Example 3

Production of Compound No. 81

4-Chlorophenoxyacetone (1.84 g), sodium cyanide (0.5 g), ammoniumchloride (0.9 g) were dissolved in methanol (10 ml), to which an excessamount of an aqueous ethylamine solution was added. The mixture wasstirred at room temperature for 2 days. After completion of thereaction, the solvent was distilled off and the residue was extractedwith ethylacetate, followed by a common procedure to obtain2-ethylamino-2-methyl-3-(4-chlorophenoxy)propanenitrile (2.2 g).

2-Ethylamino-2-methyl-3-(4-chlorophenoxy)propanenitrile (0.5 g) and4-chlorophenylacetyl chloride (0.38 g) were dissolved in THF (10 ml), towhich pyridine (0.16 g) was added and the mixture was heated underreflux for 5 hours. After cooling to room temperature, insoluble matterwas filtered and the solvent was distilled off. The resulting oil waspurified by silica gel column chromatography (ethyl acetate-hexane) toobtian the intended compound (0.16 g; yield 20%; m.p. 83-84° C.).

Example 4

Production of Compound No. 166

4-Methoxyphenylacetic acid (0.67 g) and 2-chloro-1-methylpyridiniumiodide (1.10 g) were suspended in THF (10 ml), to which triethylamine(0.50 g) was dropwise added at room temperature. After stirring for 5minutes, 2-amino-2-methyl-3-(4-chlorophenoxy)butanenitrile (0.90 g) wasadded and the mixture was stirred for 6 hours. After completion of thereaction, insoluble matter was filtered and the solvent was distilledoff. The residue was purified by silica gel column chromatography (ethylacetate-hexane) to obtain the intended compound (0.78 g; yield 52%; m.p.129-131° C.).

Example 5

Production of Compound No. 253

2-(5-Trifluoromethyl-2-pyridyl)acetic acid hydrochloride (0.74 g),2-amino-2-methyl-3-(4-trifluoromethylphenoxy)propanenitrile (0.65 g),2-chloro-1-methylpyridinium iodide (1.17 g) and triethylamine (0.93 g)were added to acetonitrile (10 ml) and heated under reflux for 6 hours.To the reaction mixture was added water and the mixture was extractedwith ethyl acetate and dried over anhydrous sodium sulfate. Thereafter,the solvent was distilled off. The residue was purified by silica gelcolumn chromatography (ethyl acetate-hexane) to obtain the intendedcompound (0.34 g; yield 28%; m.p. 97-99° C.).

Example 6

Production of Compound No. 288

3-Phenylacetylenecarboxylic acid (0.28 g),2-amino-2-methyl-3-(4-chlorophenoxy)propanenitrile (0.40 g) anddicyclohexylcarbodiimide (0.41 g) were dissolved in dichloromethane (5ml) and the solution was heated under reflux for 8 hours. The reactionmixture was filtered and the filtrate was concentrated. The residue waspurified by silica gel column chromatography (ethyl acetate-hexane) toobtain the intended compound (0.11 g; yield 17%; paste).

The agricultural and horticultural insecticide containing theaminoacetonitrile derivative of the formula (I) of the invention as anactive ingredient is suitable for controlling various pests inagriculture, forestry, horticulture, stored products as well as sanitaryvermin or nematoda which are harmful for paddy rice, fruit trees,vegetables, other crops and flowers. It has strong insecticidal effecton pests, for example, injurious insects of Lepidoptera such as summerfruit tortrix (Adoxophyes orana fasciata), smaller tea tortrix(Adoxophyes sp.), Manchurian fruit moth (Grapholita inopinata), orientalfruit moth (Grapholita molesta), soybean pod borer (Leguminivoraglycinivorella), mulberry leafroller (Olethreutesmori), tea leafrokker(Caloptilia thevivora), Caloptilia zachrysa, apple leafminer(Phyllonorycter ringoniella), pear barkminer (Spulerrina astaurota),common cabbage worm (Piers rapae crucivora), corn earworm, cottonbollworm, tabacco budworm and tomato grub (Heliothis sp.), codling moth(Laspey resia pomonella), diamondback moth (Plutella xylostella), applefruit moth (Argyresthia conjugella), peach fruit moth (Carposinaniponesis), rice stem borer (Chilo suppressalis), rice leafroller(Cnaphalocrocis medinalis), tabacco moth (Ephestia elutella), mulberrypyralid (Glyphodes pyloalis), yellow rice borer (Scirpophagaincertulas), rice skipper (Parnara guttata), rice armyworm (Pseudaletiaseparata), pink birer (Sesamia inferens), common cutworm (Spodopteralitura), beet armyworm (Spodoptera exigua); injurious insects ofHemiptera such as aster leafhopper (Macrosteles fascifrons), green riceleafhopper (Nephotettix cincticeps), brown rice planthopper (Nilaparvatalugens), whitebacked rice planthopper (Sogatella furcifera), citruspsylla (Diaphorina citri), grape whitefly (Aleurolobus taonabae), sweetpotato whitefly (Bemisia tabaci), greenhouse whitefly (Trialeurodesvaporariorum), turnip aphid (Lipaphis erysimi), green peach aphid (Myzuspersicae), Indianwax scale (Ceroplastes ceriferus), cottony cutrus scale(Pulvinaria aurantil), camphorscale (Pseudaonidia duplex), San Josescale (Comstockaspis perniciosa), arrowhead scale (Unaspis yanonesis);injurious insects of Coleoptera such as soybean beetle (Anomalarufocuprea), Japanese beetle (Popillia japonica), tabacco beetle(Lasioderma serricorne), powderpost beetle (Lyctus brunneus),twenty-eight-spotted ladybird (Epilachna vigintiotopunctata), adzukibean weevil (Callosobruchus chinensis), vegetable weevil (Listroderescostirostris), maize weevil (Sitophilus zeamais), boll weevil(Anthonomus gradis gradis), rice water weevil (Lissorhoptrusoryzophilus), cucurbit leaf beetle (Aulacophora femoralis), rice leafbeetle (Oulema oryzae), striped flea beetle (Phyllotreta striolata),pine shoot beetle (Tomicus piniperda), Colorado potate beetle(Leptinotarsa decemlineata), Mexican bean beetle (Epilachna varivestis),corn root worm (Diabrotica sp.); injurious insects of Diptera such asmelon fly (Dacus(Zeugodacus)cucurbitae), oriental fruit fly(Dacus(Bactrocera)dorsalis), rice leafminer (Agromyza oryzae), onionmaggot (Delia antiqua), seedcorn maggot (Delia platura), soybean podgall midge (Asphondylia sp.), house fly (Musca domestica), housemosquito (Culex pipiens); injurious insects of Tylenchida such asroot-lesion nematode (Pratylenchussp.), potatocyst nematode (Globoderarostochiensis), root-knot nematode (Meloidogyne sp.), citrus nematode(Tylenchulus semipenetrans), Aphelenchus avenae, chrysanthemumfoliarnematode (Aphelenchoides ritzemabosi).

The agricultural and horticultural insecticide containing theaminoacetonitrile derivative of the formula (I) of the invention hasremarkable controlling effect on the above-mentioned pests harmful topaddy field crops, farm crops, fruit trees, vegetables, and other cropsand flowers so that treatment of paddy field water, stems and leaves orsoil, such as paddy field, farm, fruit trees, vegetables, other crops,and flowers in a good timing when emergence of pests is expected andbefore emergence of pests or after their emergence is confirmed willexhibit the desired effects of the agricultural and horticulturalinsecticide of the present invention.

The agricultural and horticultural insecticide of the present inventionis generally formulated in appropriate formulation convenient for useaccording to conventional methods for the production of agriculturalchemicals before it can be used.

That is, the aminoacetonitrile derivative of the formula (I) may bemixed in an appropriate amount with a suitable inert carrier and, asrequired, with an adjuvant to conduct dissolution, dispersion,suspension, mixing, dipping, adsorption or absorption and the mixture beformulated into a suspension, an emulsion, a liquid, a wettable powder,a granule, a dust, tablets or the like.

The inert carrier which can be used in the present invention may be anyof solids or liquids. Materials which can be used as solid carriersinclude, for example, soybean flour, cereal flour, wood flour, barkflour, sawdust, tobacco stalk flour, walnut shell flour, wheat bran,cellulose fiber, residue after formation of a plant extract, syntheticpolymers such as pulverized synthetic resin, clays (for example, kaolin,bentonite, acid clay, etc.), talcs (for example, talc, pyrophillite,etc.), silicas (for example, diatomaceous earth, quartz sand, mica,white carbon (fine hydrated silicon, also referred to as silicic acidhydrate, which contains high-dispersion silicic acid; some productscontain mainly calcium silicate), activated carbon, sulfur powder,pumice stone, calcined diatomaceous earth, brick pulverization product,fly ash and sand, inorganic mineral powders such as calcium carbonate,calcium phosphate, chemical fertilizers or composts of ammonium sulfate,ammonium phosphate, ammonium nitrate, urea and ammonium chloride. Thesemay be used singly or as mixtures of two or more of them.

The liquid carrier includes one having itself a solvent effect and onefree from a solvent effect but can disperse the active ingredient usingan adjuvant. Typical examples include the following carriers, which canbe used singly or as mixtures of two or more of them, for example,water, alcohols (for example, methanol, ethanol, isopropanol, butanol,ethylene glycol, etc.), ketones (for example, acetone, methyl ethylketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.),ethers (for example, ethyl ether, dioxane, Cellosolve, dipropyl ether,tetrahydrofuran, etc.), aliphatic hydrocarbons (for example, kerosene,mineral oil, etc.), aromatic hydrocarbons (for example, benzene,toluene, xylene, solvent naphtha, alkylnaphthalen, etc.), halogenatedhydrocarbons (for example, dichloroethane, chloroform, carbontetrachloride, chlorinated benzene, etc.), esters (for example, ethylacetate, phthalate, diisopropyl phthalate, dibutyl phthalate, dioctylphthalate, etc.), amides (for example, dimethylformamide,diethylformamide, dimethylacetamide, etc.), nitriles (for example,acetonitrile, etc.), dimethyl sulfoxide, and the like.

Other adjuvants include typical adjuvants exemplified below. Theseadjuvants are used depending on the purpose and they can be used singlyor two or more of adjuvants can be used in combination. Alternatively,no adjuvant can be used in some cases.

For the purpose of emulsification, dispersion, solubilization and/orwetting of the active ingredient compound, a surfactant is used.Examples of the surfactant include, for example, polyoxyethylene alkylether, polyoxyethylene alkylaryl ether, polyoxyethylene higher fattyacid ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitanmonolaurate, polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate,naphthalenesulfonic acid condensate, ligninsulfonate, higher alcoholsulfate, etc.

The adjuvant can be used to stabilize the active ingredient compound andto adhere or bind the active ingredient compound. Examples of such anadjuvant includes casein, gelatin, starch, methyl cellulose,carboxymethylcellulose, gum Arabic, polyvinyl alcohol, wood turpentineoil, rice bran oil, bentonite, lignin sulfite liquor, etc.

The adjuvant can be used to improve fluidity of solid products. Examplesof such an adjuvant is, for example, wax, stearates, alkyl phosphates,etc.

As the deflocculated for suspension products, adjuvants such asnaphthalenesulfonic acid condensates, condensed phosphates, etc. can beused.

As the defoaming agent, adjuvants such as silicone oil can be used.

The amount of the active ingredient compound may be adjusted, ifdesired. For example, 0.01 to 50% by weight is suitable in the case ofdust or granule and 0.01 to 50% by weight is also suitable in the caseof emulsions and wettable powder.

In order to control various pests, the agricultural and horticulturalinsecticide of the present invention can be applied in an amounteffective to prevent insect damages as it is or suitably diluted with orsuspended in water or the like, to crops on which emergence of the pestsis expected or to the place where emergence of the pests is undesirable.

The amount of the agricultural and horticultural insecticide of thepresent invention may vary depending on various factors such as purpose,pests to be treated, state of growth of crops, trend of emergence ofpests, weather, environmental conditions, formulations, applicationmethods, application sites and application periods. However, it may beselected suitably depending on the purpose within the range of 0.1 g to10 kg per 10 ares as the active ingredient compound.

The agricultural and horticultural insecticide of the present inventioncan be used in combination with other agricultural and horticulturalagents for controlling diseases insect pests in order to further extenddiseases and pests, optimal controlling time or reduce doses.

Hereafter, typical examples and test examples of the present inventionwill be shown. However, the present invention is not limited thereto.

In the following formulations, all parts are parts by weight.

Formulation Example 1

Compound described in Tables 1, 2 or 3 50 parts

Xylene 40 parts

A mixture of polyoxyethylene nonyl phenyl ether and calciumalkylbenzenesulfonate 10 parts

The above ingredients are mixed and dissolved uniformly to form anemulsion.

Formulation Example 2

Compound described in Tables 1, 2 or 3 3 parts

Clay powder 82 parts

Diatomaceous powder 15 parts

The above ingredients are mixed and pulverized uniformly to form a dust.

Formulation Example 3

Compound described in Tables 1, 2 or 3 5 parts

Powder of bentonite and clay 90 parts

Calcium ligninsulfonate 5 parts

The above ingredients are mixed uniformly and kneaded after addition ofa suitable amount of water and, the mixture was granulated and dried toobtain granules.

Formulation Example 4

Compound described in Tables 1, 2 or 3 20 parts

Kaolin and synthetic highly dispersed silicic acid 75 parts

A mixture of polyoxyethylene nonyl phenyl ether and calciumalkylbenzenesulfonate 5 parts

The above ingredients are mixed and pulverized uniformly to obtain awettable powder.

Test Example 1

Insecticidal Effect Against Diamondback Moth (Plutella xylostella)

On a seedling of a Chinese cabbage was left to adult of diamondback moth(Plutella xylostella) for breeding and allowed to lay eggs and two daysafter the start of breeding, the seedling of a Chinese cabbage on whichthe eggs are deposited was dipped in a chemical liquid prepared bydiluting a chemical agent containing a compound described in Table 1,Table 2 or Table 3 to 500 ppm for 30 seconds. After air drying, theseedling was left to stand in a thermostatic chamber at 25° C . After 6days from the dipping in the chemical solution, the number of hatchedinsects was examined. The mortality of insects was calculated by thefollowing formula and determination was made according to the followingstandards. 1 Lot, 10 insects, 3 series system.

Corrected insect mortality (%)

Number of hatched insects of no treatment lot−number of hatched insectsof treated lot=Number of hatched insects of no treated lot

Standards of determination:

A: Dead insect ratio 100%

B: Dead insect ratio 99 to 90%

C: Dead insect ratio 89 to 80%

D: Dead insect ratio 79 to 50%

The results obtained are shown in Table 5.

Test Example 2

Insecticidal Effect Against Smaller Tea Tortrix (Adoxophyes sp.)

Tea leaves (variety: Yabukita) were dipped in a chemical liquid preparedby diluting a chemical agent containing a compound described in Table 1,Table 2 or Table 3 to 500 ppm for 30 seconds. After air drying, theywere placed in a plastic dish of 9 cm in diameter, in which 2nd instarlarvae of smaller tea tortrix (Adoxophyes sp.) were inoculated.Thereafter, the dish was covered with a lid and left to stand athermostatic chamer at 25° C. and at a humidity of 70%. After 8 daysfrom the inoculation, the mortarity number of the insects were examinedand determination was made in accordance with the Test Example 1. 1 Lot,10 insects, 3 series system.

The results obtained are shown in Table 5.

TABLE 5 Com- Test Test Test Test pound Example Example Compound ExampleExample No. 1 2 No. 1 2 2 A A 49 B 3 A 52 A A 12 A 53 A A 13 A A 54 A 14A A 55 A 21 A A 57 A A 22 A 60 A A 23 A A 62 A A 24 A A 64 A A 25 A 66 AA 26 A A 67 A D 27 A 68 A 28 A A 69 A A 29 A 73 A A 30 A A 74 A A 41 A A75 A A 42 A 76 A 46 A 77 A 48 A A 79 A A 80 A A 141 A A 81 A A 143 A A83 A A 146 A A 84 B 147 A A 91 A 148 A A 92 A A 149 A A 94 A A 150 A A95 A A 151 A A 96 A A 153 A A 97 A A 156 A A 100 A A 157 A A 105 A A 163A 108 A 165 A A 114 A A 173 A A 116 A A 174 A 118 C 176 A 121 A A 184 A122 A A 186 A A 123 A A 188 A A 124 A A 187 A A 126 A A 189 A A 128 A190 A A 191 A A 245 A 195 A A 253 A A 196 A A 269 A A 197 A 270 A A 200A A 271 A 207 A A 278 A 209 A A 279 A A 220 A A 280 A 221 A 282 A A 223A 283 A C 224 A 284 A A 229 A A 285 A A 231 A A 286 A 232 A A 293 A A233 A A 294 A A 234 C 296 A 235 A A 299 A 236 A A 306 A A 237 A A 307 A238 A A 309 A A 243 A A 310 A A 244 A 311 A A 312 A A 350 A 313 A A 351A 314 A 353 A 316 A A 354 A 317 A 355 A 318 A A 356 A 319 A A 359 A 320A 362 A 321 A A 363 A 322 A 366 A A 324 A 369 A A 325 A 326 A 327 A 328A A 333 A 336 A A 337 A 339 A 342 A A 348 A 349 A

What is claimed is:
 1. An aminoacetonitrile derivative of the formula(I):

(wherein Ar¹ and Ar² may be the same or different and each represents aphenyl group; a substituted phenyl group having at least one substituentwhich may be the same or different and selected from the group of ahalogen atom, a nitro group, a cyano group, a C₁-C₆ alkyl group, a haloC₁-C₆ alkyl group, a C₁-C₆ alkoxy group, a halo C₁-C₆ alkoxy group, aC₂-C₆ alkenyl group, a halo C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group,a C₃-C₆ cycloalkyl group, a C₂-C₆ alkenyloxy group, a halo C₂-C₆alkenyloxy group, a C₁-C₆ alkylthio group, a halo C₁-C₆ alkylthio group,a C₁-C₆ alkylsulfonyloxy group, a halo C₁-C₆ alkylsulfonyloxy group, aC₁-C₆ alkylsulfinyl group, a halo C₁-C₆ alkylsulfinyl group, a C₁-C₆alkylsulfonyl group, a halo C₁-C₆ alkylsulfonyl group, a C₂-C₆alkenylthio group, a halo C₂-C₆ alkenylthio group, a C₂-C₆alkenylsulfinyl group, a halo C₂-C₆ alkenylsulfinyl group, a C₂-C₆alkenylsulfonyl group, a halo C₂-C₆ alkenylsulfonyl group, a C₁-C₆alkylamino group, a di-C₁-C₆ alkylamino group, a C₁-C₆alkylsulfonylamino group, a halo C₁-C₆ alkylsulfonylamino group, a C₁-C₆alkylcarbonyl group, a halo C₁-C₆ alkylcarbonyl group, a C₁-C₆alkyloxycarbonyl group, a phenyl group, a substituted phenyl grouphaving at least one substituent which may be the same or different andselected from the group consisting of a halogen atom, a cyano group, anitro group, a C₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₆alkoxy group, a halo C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a haloC₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo C₁-C₆alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group and a halo C₁-C₆alkylsulfonyl group, a phenyloxy group, a substituted phenyloxy grouphaving on the ring thereof at least one substituent which may be thesame or different and selected from the group consisting of a halogenatom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo C₁-C₆alkyl group, a C₁-C₆ alkoxy group, a halo C₁-C₆ alkoxy group, a C₁-C₆alkylthio group, a halo C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinylgroup, a halo C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group anda halo C₁-C₆ alkylsulfonyl group, a phenylacetylene group, or asubstituted phenylacetylene group having on the ring thereof at leastone substituent which may be the same or different and selected from thegroup consisting of a halogen atom, a cyano group, a nitro group, aC₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₆ alkoxy group, ahalo C₁-C₆ alkoxy group, a C₁-C₆ alkylthio, group, a halo C₁-C₆alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo C₁-C₆ alkylsulfinylgroup, a C₁-C₆ alkylsulfonyl group and a halo C₁-C₆ alkylsulfonyl group,a pyridyloxy group and a substituted pyridyloxy group having on the ringthereof at least one substituent which may be the same or different andselected from the group consisting of a halogen atom, a cyano group, anitro group, a C₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₆alkoxy group, a halo C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a haloC₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo C₁-C₆alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group and a halo C₁-C₆alkylsulfonyl group; Q represents a group of

(wherein R¹ and R² may be the same or different and each represent ahydrogen atom, a halogen atom, a C₁-C6 alkyl group, a halo C₁-C₆ alkylgroup, a C₁-C₆ alkoxy group, a halo C₁-C₆ alkoxy group, a C₃-C₆cycloalkyl group, or a substituted C₃-C₆ cycloalkyl group having atleast one substituent which may be the same or different and selectedfrom the group consisting of a halogen atom and a C₁-C₆ alkyl group, andR₁ and R₂ may be bound to represent a C₂-C₆ alkylene group which mayhave on its chain at least one substituent selected from the groupconsisting of a halogen atom, a C₁-C₆ alkyl group and a C₁-C₆ alkoxygroup), —CH═CH— or —C≡C—; d is 0 or an integer of 1; R₃ represents ahydrogen atom, a C₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a cyanoC₁-C₆ alkyl group, a C₁-C₆ alkylthio group, a halo C₁-C₆ alkylthiogroup, a C₂-C₆ alkenyl group or a C₂-C₆ alkynyl group; R₄, R₅, R₆, R₇and R₈ which may be the same or different and each represents a hydrogenatom, a halogen atom, a C₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, aC₃-C₆ cycloalkyl group, a substituted C₃-C₆ cycloalkyl group having atleast one substituent which may be the same or different and selectedfrom the group consisting of a halogen atom and a C₁-C₆ alkyl group, aphenyl group or a substituted phenyl group having at least onesubstituent group which may be the same or different and selected fromthe group consisting of a halogen atom, a nitro group, a cyano group, aC₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₆, alkoxy group, ahalo C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo C₁-C₆ alkylthiogroup, a C₁-C₆ alkylsulfinyl group, a halo C₁-C₆ alkylsulfinyl group, aC₁-C₆ alkylsulfonyl group, a halo C₁-C₆ alkylsulfonyl group, a C₁-C₆alkylamino group and a di-C₁-C₆ alkylamino group, and R₄ and R₆ togethermay form a C₁-C₆ alkylene group; W is —O—, —S—, —SO₂,—, or —N(R⁹)—(wherein R⁹ is a hydrogen atom or a C₁-C₆ alkyl group), and a and b maybe the same or different and a is an integer from 1 to 4 and b is 0 oran integer from 1 to 4)).
 2. An aminoacetonitrile derivative as claimedin claim 1, wherein Ar¹ and Ar² represent a phenyl group; a substitutedphenyl group having at least one substituent which may be the same ordifferent and selected from the group of a halogen atom, a cyano group,a nitro group, a C₁-C₆, alkyl group, a halo C₁-C₆ alkyl group, a C₂-C₆alkenyl group, a halo C₂-C₆, alkenyl group, a C₂-C₆ alkynyl group, aC₃-C₆ cycloalkyl group, a C1-C6 alkoxy group, a halo C₁-C₆ alkoxy group,a C₂-C₆ alkenyloxy group, a halo C₂-C₆ alkenyloxy group, a C₁-C₆alkylsulfonyloxy group, a halo C₁-C₆, alkylsulfonyloxy group, a C₁-C₆alkylthio group, a halo C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinylgroup, a halo C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, ahalo C₁-C₆, alkylsulfonyl group, a C₂-C₆ alkenylthio group, a halo C₂-C₆alkenylthio group, a C₂-C₆ alkenylsulfinyl group, a halo C₂-C₆alkenylsulfinyl group, a C₂-C₆ alkenylsulfonyl group, a halo C₂-C₆alkenylsulfonyl group, a C₁-C₆ alkylamino group, a di-C₁-C₆ alkylaminogroup, a C₁-C₆ alkylsulfonylamino group, a halo C₁-C₆ alkylsulfonylaminogroup, a C₁-C₆ alkylcarbonyl group, a halo C₁-C₆ alkylcarbonyl group, aC₁-C₆ alkyloxycarbonyl group, a phenyl group, a substituted phenyl grouphaving at least one substituent which may be the same or different andselected from the group consisting of a halogen atom, a cyano group, anitro group, a halo C₁-C₆ alkyl group, a halo C₁-C₆ alkoxy group, a haloC₁-C₆ alkylsulfonyloxy group, a halo C₁-C₆ alkylthio group, a halo C₁-C₆alkylsulfinyl group and a halo C₁-C₆ alkylsulfonyl group, a phenyloxygroup, a substituted phenyloxy group having on the ring thereof at leastone substituent which may be the same or different and selected from thegroup consisting of a halogen atom, a cyano group, a nitro group, a haloC₁-C₆ alkyl group, a halo C₁-C₆ alkoxy group, a halo C₁-C₆ alkylthiogroup, a halo C₁-C₆ alkylsulfinyl group and a halo C₁-C₆ alkylsulfonylgroup, a phenylacetylene group, or a substituted phenylacetylene grouphaving on the ring thereof at least one substituent which may be thesame or different and selected from the group consisting of a halogenatom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo C₁-C₆alkyl group, a C₁-C₆ alkoxy group” a halo C₁-C₆ alkoxy group, a C₁-C₆alkylthio group, a halo C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinylgroup, a halo C₁-C₆ alkylsulfinyl group, C₁-C₆ alkylsulfonyl group and ahalo C₁-C₆ alkylsulfonyl group, a pyridyloxy group, and a substitutedpyridyloxy group having on the ring thereof at least one substituentwhich may be the same or different and selected from the groupconsisting of a halogen atom, a cyano group, a nitro group, a halo C₁-C₆alkyl group, a halo C₁-C₆ alkoxy group, a halo C₁-C₆ alkylthio group, ahalo C₁-C₆ alkylsulfinyl group and a halo C₁-C₆ alkylsulfonyl group; Qrepresents a group of

(wherein R₁ and R₂ may be the same or different and each represent ahydrogen atom, a halogen atom, a C₁-C₆ alkyl group, a halo C₁-C₆ alkylgroup or a C₁-C₆ alkoxy group, and R₁ and R₂ may be bound to represent aC₂-C₆ alkylene group which may have on its chain at least onesubstituent selected from the group consisting of a halogen atom, aC₁-C₆ alkyl group or a C₁-C₆, alkoxy group), —CH═CH— or —C≡C—; d is 0 oran integer of 1; R₃ represents a hydrogen atom, a C₁-C₆, alkyl group, ahalo C₁-C₆, alkyl group, a C₂-C₆, alkenyl group or a C₂-C₆ alkynylgroup; R₄, R₅, R₆, R₇ and R₈ which may be the same or different and eachrepresents a hydrogen atom, a C₁-C₆ alkyl group, a halo C₃-C₆, alkylgroup, a C₃-C₆ cycloalkyl group, or a substituted C₃-C₆ cycloalkyl grouphaving at least one substituent which may be the same or different andselected from the group consisting of a halogen atom and a C₁-C₆, alkylgroup, and R₄ and R₅ together may form a C₁-C₆ alkylene group; W is —O—,—S—, —SO2— or —N(R₉)— (wherein R₉ is a hydrogen atom or a C₁-C₆, alkylgroup), and a and b may be the same or different and a is an integerfrom 1 to 4 and b is 0 or an integer from 1 to 4)).
 3. Anaminoacetonitrile derivative as claimed in claim 2, wherein Ar¹ and Ar²represent a phenyl group; a substituted phenyl group having at least onesubstituent which may be the same or different and selected from thegroup of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkylgroup, a halo C₁-C₆ alkyl group, a C₁-C₆ alkoxy group, a halo C₁-C₆alkoxy group, a C₁ C₆ alkenyloxy group, a halo C₂-C₆ alkenyloxy group, aC₁-C₆ alkylthio group, a halo C₁-C₆ alkylthio group, a C₁-C₆alkylsulfonyl group, a halo C₁-C₆ alkylsulfonyl group, a C₂-C₆alkenylthio group, a halo C₂-C₆ alkenylthio group, a C₂-C₆alkenylsulfonyl group, a halo C₂-C₆ alkenylsulfonyl group, a C₁-C₆alkyloxycarbonyl group, a phenyl group, a substituted phenyl grouphaving at least one substituent which may be the same or different andselected from the group consisting of a halogen atom, a cyano group, anitro group, a halo C₁-C₆ alkyl group, a halo C₁-C₆ alkoxy group, a haloC₁-C₆ alkylthio group and a halo C₁-C₆ alkylsulfonyl group, a phenyloxygroup, a substituted phenyloxy group having on the ring thereof at leastone substituent which may be the same or different and selected from thegroup consisting of a halogen atom, a cyano group, a nitro group, a haloC₁-C₆ alkyl group, a halo C₁-C₆ alkoxy group, a halo C₁-C₆ alkylthiogroup and a halo C₁-C₆ alkylsulfonyl group, a phenylacetylene group, ora substituted phenylacetylene group having on the ring thereof at leastone substituent which may be the same or different and selected from thegroup consisting of a halogen atom, a cyano group, a nitro group, a haloC₁-C₆ alkyl group, a halo C₁-C₆ alkoxy group, a halo C₁-C₆ alkylthiogroup and a halo C₁-C₆ alkylsulfonyl group, Q represents a group of(wherein R₁ and R₂ may be the same or different and each represent ahydrogen atom, a halogen atom, a C₁-C₆ alkyl group, a halo C₁-C₆, alkylgroup or a C₁-C₆ alkoxy group, and R¹ and R² may be bound to represent aC₂-C₆ alkylene group which may have on its chain at least onesubstituent selected from the group consisting of a halogen atom, aC₁-C₆ alkyl group and a C₁-C₆ alkoxy group), —CH≡CH— or —C≡C—; d is 0 oran integer of 1; R³ represents a hydrogen atom, a C,—C, alkyl group, ahalo C₁-C₆ alkyl group, a C₂-C₆ alkenyl group or a C₂-C₆ alkynyl group;R⁴, R⁵, R⁶, R⁷ and R⁸ which may be the same or different and eachrepresents a hydrogen atom, a C₁-C₆ alkyl group, a halo C₁-C₆ alkylgroup, a C₃-C₆ cycloalkyl group or a substituted C₃-C₆ cycloalkyl grouphaving at least one substituent which may be the same or different andselected from the group consisting of a halogen atom and a C₁-C₆ alkylgroup, and R⁴ and R⁵ together may form a C₁-C₆ alkylene group; W is —O—,—S—, —SO₂ — or —N(R⁹)— (wherein R⁹ is a hydrogen atom or a C₁-C₆ alkylgroup), and a and b may be the same or different and a is an integerfrom 1 to 4 and b is 0 or an integer from 1 to 4)).
 4. An agriculturaland horticultural pesticide composition containing as an activeingredient the aminoacetonitrile derivative as claimed in claim
 3. 5. Amethod of combating pests using an agricultural and horticulturalpesticide, the method comprising applying an effective amount of theagricultural and horticultural pesticide composition as claimed in claim4 to useful plants for the protection of the useful plants.
 6. Theaminoacetonitrile derivative of claim 1, wherein Ar¹ and Ar² may be thesame or different and each represents a phenyl group.
 7. Theaminoacetonitrile derivative of claim 1, wherein Ar¹ and Ar² may be thesame or different and each represents a substituted phenyl group havingat least one substituent which may be the same or different and selectedfrom the group of a halogen atom, a nitro group, a cyano group, a C₁-C₆alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₁ alkoxy group, a haloC₁-C₁alkoxy group, a C₂-C₆ alkenyl group, a halo C₂-C₆ alkenyl group, aC₂-C₆ alkynyl group, a C₃-C₆ cycloalkyl group, a C₂-C₆ alkenyloxy group,a halo C₂-C₆ alkenyloxy group, a C₁-C₆ alkylthio group, a halo C₁-C₆alkylthio group, a C₁-C₆ alkylsulfonyloxy group, a halo C₁-C₆alkylsulfonyloxy group, a C₁-C₆ alkylsulfinyl group, a halo C₁-C₆alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo C₁-C₆alkylsulfonyl group, a C₂-C₆ alkenylthio group, a halo C₂-C₆ alkenylthiogroup, a C₂-C₆ alkenylsulfinyl group, a halo C₂-C₆ alkenylsulfinylgroup, a C₂-C₆ alkenylsulfonyl group, a halo C₂-C₆ alkenylsulfonylgroup, a C₁-C₆ alkylamino group, a di-C₁-C₆ alkylamino group, a C₁-C₆alkylsulfonylamino group, a halo C₁-C₆ alkylsulfonylamino group, a C₁-C₆alkylcarbonyl group, a halo C₁-C₆ alkylcarbonyl group, a C₁-C₆alkyloxycarbonyl group, a phenyl group, a substituted phenyl grouphaving at least one substituent which may be the same or different andselected from the group consisting of a halogen atom, a cyano group, anitro group, a C₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₆alkoxy group, a halo C₁-C₆ alkoxy group, a C₁-C₁alkylthio group, a haloC₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo C₁-C₆alkylsulfinyl group, a C₁-C₁alkylsulfonyl group and a halo C₁-C₆alkylsulfonyl group.
 8. The aminoacetonitrile derivative of claim 1,wherein Ar¹ and Ar² may be the same or different and each represents aphenyloxy group.
 9. The aminoacetonitrile derivative of claim 1, whereinAr¹ and Ar² may be the same or different and each represents asubstituted phenyloxy group having on the ring thereof at least onesubstituent which may be the same or different and selected from thegroup consisting of a halogen atom, a cyano group, a nitro group, aC₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₆ alkoxy group, ahalo C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo C₁-C₆ alkylthiogroup, a C₁-C₆ alkylsulfinyl group, a halo C₁-C₆ alkylsulfinyl group, aC₁-C₆ alkylsulfonyl group and a halo C₁-C₆ alkylsulfonyl group.
 10. Theaminoacetonitrile derivative of claim 1, wherein Ar¹ and Ar² may be thesame or different and each represents a phenylacetylene group.
 11. Theaminoacetonitrile derivative of claim 1, wherein Ar¹ and Ar² may be thesame or different and each represents a substituted phenylacetylenegroup having on the ring thereof at least one substituent which may bethe same or different and selected from the group consisting of ahalogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a haloC₁-C₆ alkyl group, a C₁-C₆ alkoxy group, a halo C₁-C₆ alkoxy group, aC₁-C₆ alkylthio, group, a halo C₁-C₆ alkylthio group, a C₁-C₆alkylsulfinyl group, a halo C₁-C₆ alkylsulfinyl group, a C₁-C₆alkylsulfonyl group and a halo C₁-C₆ alkylsulfonyl group, a pyridyloxygroup and a substituted pyridyloxy group having on the ring thereof atleast one substituent which may be the same or different and selectedfrom the group consisting of a halogen atom, a cyano group, a nitrogroup, a C₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₁-C₆ alkoxygroup, a halo C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo C₁-C₆alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo C₁-C₆ alkylsulfinylgroup, a C₁-C₆ alkylsulfonyl group and a halo C₁-C₆ alkylsulfonyl group.